Treatment of rubber



ranaminoal lamina or dial lamino ou Patented July 19, 1932 V or];

ramm ng." V

This invention relatesto the treatment of and particularly 1 to accelerating the 'vulcanization of the same withamino acridines'.

An object of this invention is to provide a new class of tion of rubber. Afurther object is to provide a class of acceleratorswhich function Well in stocks containing more than 30 parts, by weight of carbon black "per 100 her, that is, such as tire tread stocks;

Accordingly the invention comprises vul canizin'g rubber in the presence of an amino acridine and preferably'one having hydrogen attached to the carbon atom in" the 5-position and in which an amino group is attached to each of the benzene nuclei. The amino groups may be primary amino; groups or monoalkyl or dialkyl 'substituted amino.

groups. The acridinering may be further substituted in any position 5-position by other groups such as alkyl or halogen groups. p Y a 7 he amino acridines of the kind described may be represented by th'e structural formula J (P n jl wherein R and R' represent ortho-arylene ea'ch contain f groups, and" WhereinvR' and R attached to the aromatic nucleus.

The subs tituents are numbered according to their positions, as indi cated in the following diagram of the acridinelring:

i jig is believed that wheiifthe se .bodies are used in rubber, rubber and similar"vulca-nizable materials' th accelerators for the vulcaniza parts of rubother than the 7 uterine Application nleau n 31,1930." serial no. 440,629;

e vulcanization, between I sulfur: and (the 'acridine compo'und'at the fi-"po nwfi rglving athio. body Which as the actual as 2,8 diamino-3,7 dirnethyl dimethylamino 'acridine; tetra" 1nethy1fjdiamino ""acridine' j 7 -aInino-3- methylamino-8 methyl acridine 9-aminofi-dimethylaminodiamino-Q-methyl acridine.

The structure dine would correspond to 1. V

6 chloro acridine,3,7'-di amino acridine; 3,7

The following examples i i are by weight tion and are not to be are illustrative of thef'inven- ;;EwampZ e-A.+' I' mix onthe mill in the usual mannerIIpa-rtf f diarninddimethyl i V "lacridine witha typical tread ing 100. parts;

stock contain- ;of smoked sheet probably functions accelerator. This "conclusion 71s based on the fact'thatwhen a substituted 4 acridine "having hydrogen as the substituent in the 5-positionis,warmed-yvith-sulfur ata 0f,diamino acriconstrued L as; liin'itin'g rubber; ""Sa-m- H ples of 1 this stock are; vulcanized in? a-inbld' aireaction takes-place, during (T representstensfle strength and E represents per cent rate; stockand. are. not. '60 i under 45 pounds steam pressure for 45, 60, -7 5, and 90 minutes and are then found to be well cured and give the following tensiles in pounds per sq. in. r

Stock containing diamino dime acrldine 3725:& 520% (T; represents tensile strength and E represents oer cent elongation at break.) a F .In the absence cally 'sile strength being approximately I200 lbs.- per sq. -in. after heating under similar.- conditions. y j Example B -%100 parts of; pale crepe rub her, 101parts' zinc oxide,3 parts of sulfur and .5. parts: of diamino dimethyl acri-dine are .mixed on the mill in theusualf nanner.v This mix isrvulcanizedin a mold under 40 pounds steam pressure ior and 6(Jfminutes and the following tensiles are; obtained: I i I of the accelerator practi Stock containing diammo dlmeth sell me I Cure (T'ren esents tensile-strength and E represents he: cent elongation at break.) Q I r I In a'si'rnilanstock 7 contain ng no accelerator, no vulcanization, takes place under similar conditions. i c f Example 0.Wh81il 1 part of tetra methyl diamino acridine is substituted for diamino dimethylacridine in theabove tre'ad forv mula, it gives the following tensiles Stock containing tetramethyl diamino. acridine elongation at break.) s

The; chemicals disclosed may be used for 7 acceleration of Yulcanization of any type-of M c e-refin d mixes containing carbon black. l W

Although. certain thwries tes-5am 419i a; mode of. reaction duringivulcanination V theiinventionis"not-to. I bQ-. I1$t13ued asxconfined thereto butristo j .coventheefiect whatever theactualmode of e. d an e .h reim:

' comprisesl treating 40% 7 no vulcanization takes place,,-the ten-,

action of the acridine. It is further obvious that, from the detailed disclosure above given, modifications will suggest themselves without departing from the principle of the invention, and't is not desired to limit the invention otherwise than as set forth in the appended claims.

Having thus described my invention, what I claim and desire toprotect-by ent is:

Letters Pat- 1'. A process for I I rubber with avulcanizing agent and an amino acridine.

' i 2; process for vulcanizing rubber which "comprisestreating-rubber with a vulcanizing agent and a idiamino 'acridine "having' an amino group attached to each of the benzene nuclei;

. 3. A processiorvulcanizing rubber which com rises treatingrubber with sulphur and "a diaminoacridineihaving an amino group I attached :to each ofthe hydrogen attachedto carbon in the 5 -posibenzene nuclei; and

4. process-which comprises vulcanizing rubber. stock containing a metallic oxide and a vulcanizingagent 1n thepresence of a d1- amino acridine which hashydrogen attached carbon 1n 7 the 5-posi-tion.

5. A process whichjcomprisesvulcani zing a rubber. stock 'containingrzlnc-oxide and lsulphu r in the presence of an-alkyl diamino acridine which hashydrogen attached to carbon inthe5fi-position.,

ing a rubber'stock containing zinc oxideand vulcanizing rubber which .c .61. A .process which, comprises vulcaniz- 1100.

sulphur in thep'resenceof adiamino dimethyl "acridine which has hydrogen attachedto carbon in the 5-posit1on;

7 71A process which comprises vulcanizing a rubberstock containing zinc oxide and sulphurl in the presence rof2,8-diamino-8,' 7-dimethyl acridine. I V, I 1'' I a 8.; A.;vulcanized1-rubber product derived irom' rubber treated-with avulcani zi'ng' ag ts and an amino acr1d1ne j u 9. A vulcanized rubber product derived from-rubber treated-with a metallic oxide, a,

vulcanizing agent,and adiamino acridine 1n which hydrogen is attached to carbon in the 5-130S1ti0n.'.,.

10; A vulcaniizedrubber Q W from rubber treated-with zinc. oxide, s'ulphur and an alkyl diaminoacridinehaving hydro n attachedto carbon in the 5-p0siti0n:

11. A' vulcanized rubber product #derived from rubber treated "with zinc oxide, sulphur and a diaminodimethyl acridine having hydrogen' attached to, carbon in the 5-position.

12. A vulcanized rubber product derived from rubber'treate'd with zinc oxide, sulphur and 2,8 diamino 3,7?dirnethyl acridine. V

- I ,13. Atire tread stock derived from rubbertreated with a vulcanizingagent, a metallic I ox de, at least- 3 0' partsby weightof carbonl black per lQO parts of rubber, and an acceler- I ator comprising a diamino'acridine having an amino group attached to zene nuclei and hydrogen attached to carbon in the 5-position.

14. A tire tread stock derived from rlibber treated with sulphur, zinc oxide, at least 30 parts by Weight of carbon black per parts of rubber, and an accelerator compris- 7 ing. 2,8-diamino-3,7-dimethy1 acrldine.

Signed at Passaic, county of Passaic, State of N eW Jersey, this 21st day of March, 1930.

LOUIS H. HOWLAND.

each of the ben- 

